# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bpy-11
_database_code_depnum_ccdc_archive 'CCDC 2288367'
loop_
_audit_author_name
_audit_author_address
ffg
;grfrf
China
;
_audit_update_record             
;
2023-08-13 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;
_audit_creation_date             2023-08-12
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 Cl N4 O'
_chemical_formula_sum            'C22 H19 Cl N4 O'
_chemical_formula_weight         390.86
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Cl'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.01670(10)
_cell_length_b                   16.8651(2)
_cell_length_c                   18.0753(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1834.14(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6462
_cell_measurement_temperature    120.01(11)
_cell_measurement_theta_max      74.0770
_cell_measurement_theta_min      3.5930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.012
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9702
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.326
_diffrn_reflns_theta_min         3.584
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  23.00   0.50    0.50    --    0.00 -77.00 -90.00  130
  2  ω    -32.00   8.00   0.50    0.50    --    0.00 -82.00-180.00   80
  3  ω    -27.00  -2.00   0.50    0.50    --    0.00 -82.00-150.00   50
  4  ω     22.00 127.00   0.50    0.50    --   95.80 -82.00-180.00  210
  5  ω     68.00 105.00   0.50    0.50    --   95.80 -82.00 120.00   74
  6  ω    150.00 175.00   0.50    0.50    --   95.80  30.00 -60.00   50
  7  ω     77.00 103.00   0.50    0.50    --   95.80 -82.00 150.00   52
  8  ω     76.00 112.00   0.50    0.50    --   95.80 -82.00  90.00   72
  9  ω     16.00 109.00   0.50    0.50    --   95.80 -15.00 -60.00  186
 10  ω      6.00 112.00   0.50    0.50    --   95.80 -30.00-150.00  212
 11  ω      7.00 111.00   0.50    0.50    --   95.80 -61.00-180.00  208
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0270699000
_diffrn_orient_matrix_UB_12      -0.0783368000
_diffrn_orient_matrix_UB_13      -0.0428832000
_diffrn_orient_matrix_UB_21      -0.0035917000
_diffrn_orient_matrix_UB_22      0.0463743000
_diffrn_orient_matrix_UB_23      -0.0734492000
_diffrn_orient_matrix_UB_31      0.2545427000
_diffrn_orient_matrix_UB_32      -0.0076218000
_diffrn_orient_matrix_UB_33      -0.0056592000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                3513
_reflns_number_total             3654
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1394 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.018(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3654
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+0.2686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0763
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16), C19(H19),
 C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.07783(9) 0.75053(3) 0.35013(3) 0.03114(15) Uani 1 1 d . . . . .
O1 O 0.5210(2) 0.53060(9) 0.61047(8) 0.0266(3) Uani 1 1 d . . . . .
N1 N 0.8803(3) 0.50078(10) 0.57288(9) 0.0180(3) Uani 1 1 d . . . . .
N2 N 0.9284(3) 0.37984(10) 0.63353(9) 0.0196(4) Uani 1 1 d . . . . .
N3 N 0.8499(3) 0.39961(10) 0.45638(9) 0.0200(3) Uani 1 1 d . . . . .
N4 N 0.6473(4) 0.34147(12) 0.27658(10) 0.0283(4) Uani 1 1 d . . . . .
C1 C 0.9248(4) 0.56380(12) 0.52268(10) 0.0191(4) Uani 1 1 d . . . . .
C2 C 1.1336(4) 0.56793(14) 0.48947(12) 0.0245(5) Uani 1 1 d . . . . .
H2 H 1.245058 0.530623 0.502639 0.029 Uiso 1 1 calc R U . . .
C3 C 1.1802(4) 0.62598(14) 0.43739(12) 0.0271(5) Uani 1 1 d . . . . .
H3 H 1.322609 0.628097 0.414811 0.032 Uiso 1 1 calc R U . . .
C4 C 1.0191(4) 0.68074(13) 0.41837(11) 0.0241(4) Uani 1 1 d . . . . .
C5 C 0.8142(4) 0.67961(13) 0.45282(12) 0.0273(5) Uani 1 1 d . . . . .
H5 H 0.705682 0.718495 0.440912 0.033 Uiso 1 1 calc R U . . .
C6 C 0.7670(4) 0.62123(14) 0.50511(12) 0.0253(5) Uani 1 1 d . . . . .
H6 H 0.626290 0.620609 0.528936 0.030 Uiso 1 1 calc R U . . .
C7 C 0.6851(3) 0.48814(13) 0.60945(11) 0.0205(4) Uani 1 1 d . . . . .
C8 C 0.7052(3) 0.41036(13) 0.65061(11) 0.0200(4) Uani 1 1 d . . . . .
H8 H 0.589270 0.372264 0.633038 0.024 Uiso 1 1 calc R U . . .
C9 C 0.6935(4) 0.41907(14) 0.73544(12) 0.0259(5) Uani 1 1 d . . . . .
H9A H 0.719905 0.474621 0.750811 0.031 Uiso 1 1 calc R U . . .
H9B H 0.547707 0.401413 0.754735 0.031 Uiso 1 1 calc R U . . .
C10 C 0.8804(4) 0.36477(14) 0.76186(12) 0.0269(5) Uani 1 1 d . . . . .
H10A H 0.935803 0.381297 0.811067 0.032 Uiso 1 1 calc R U . . .
H10B H 0.829977 0.308961 0.764549 0.032 Uiso 1 1 calc R U . . .
C11 C 1.0580(4) 0.37525(14) 0.70289(11) 0.0240(4) Uani 1 1 d . . . . .
H11A H 1.144164 0.424473 0.711146 0.029 Uiso 1 1 calc R U . . .
H11B H 1.161219 0.329539 0.702150 0.029 Uiso 1 1 calc R U . . .
C12 C 1.0225(3) 0.42975(12) 0.57536(10) 0.0189(4) Uani 1 1 d . . . . .
H12 H 1.178265 0.445035 0.588402 0.023 Uiso 1 1 calc R U . . .
C13 C 1.0199(3) 0.38507(12) 0.50178(10) 0.0191(4) Uani 1 1 d . . . . .
C14 C 1.1845(4) 0.32963(13) 0.48688(12) 0.0229(4) Uani 1 1 d . . . . .
H14 H 1.302750 0.321033 0.520783 0.027 Uiso 1 1 calc R U . . .
C15 C 1.1724(4) 0.28712(13) 0.42136(12) 0.0241(4) Uani 1 1 d . . . . .
H15 H 1.281380 0.248284 0.409825 0.029 Uiso 1 1 calc R U . . .
C16 C 0.9991(4) 0.30212(12) 0.37305(11) 0.0222(4) Uani 1 1 d . . . . .
H16 H 0.987595 0.274008 0.327672 0.027 Uiso 1 1 calc R U . . .
C17 C 0.8417(4) 0.35925(12) 0.39215(11) 0.0200(4) Uani 1 1 d . . . . .
C18 C 0.6543(3) 0.38003(12) 0.34170(11) 0.0212(4) Uani 1 1 d . . . . .
C19 C 0.4970(4) 0.43636(13) 0.36191(11) 0.0241(4) Uani 1 1 d . . . . .
H19 H 0.509122 0.463633 0.407717 0.029 Uiso 1 1 calc R U . . .
C20 C 0.3222(4) 0.45215(14) 0.31418(12) 0.0276(5) Uani 1 1 d . . . . .
H20 H 0.210767 0.489500 0.327275 0.033 Uiso 1 1 calc R U . . .
C21 C 0.3126(4) 0.41242(15) 0.24681(13) 0.0306(5) Uani 1 1 d . . . . .
H21 H 0.195043 0.421828 0.212828 0.037 Uiso 1 1 calc R U . . .
C22 C 0.4791(4) 0.35900(14) 0.23100(12) 0.0317(5) Uani 1 1 d . . . . .
H22 H 0.474214 0.332792 0.184506 0.038 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.741(2) . ?
O1 C7 1.220(3) . ?
N1 C1 1.423(3) . ?
N1 C7 1.364(2) . ?
N1 C12 1.473(3) . ?
N2 C8 1.471(3) . ?
N2 C11 1.478(2) . ?
N2 C12 1.461(2) . ?
N3 C13 1.334(3) . ?
N3 C17 1.347(3) . ?
N4 C18 1.345(3) . ?
N4 C22 1.338(3) . ?
C1 C2 1.394(3) . ?
C1 C6 1.393(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(3) . ?
C4 C5 1.382(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.513(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.542(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.526(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.520(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12 1.0000 . ?
C12 C13 1.529(3) . ?
C13 C14 1.389(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.395(3) . ?
C17 C18 1.492(3) . ?
C18 C19 1.390(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.391(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.377(4) . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C12 121.16(16) . . ?
C7 N1 C1 126.00(17) . . ?
C7 N1 C12 110.99(16) . . ?
C8 N2 C11 108.77(15) . . ?
C12 N2 C8 107.65(16) . . ?
C12 N2 C11 115.86(16) . . ?
C13 N3 C17 117.77(18) . . ?
C22 N4 C18 117.1(2) . . ?
C2 C1 N1 118.80(18) . . ?
C6 C1 N1 122.43(19) . . ?
C6 C1 C2 118.77(19) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 Cl1 119.06(17) . . ?
C5 C4 Cl1 120.65(18) . . ?
C5 C4 C3 120.3(2) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 120.5(2) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O1 C7 N1 127.76(19) . . ?
O1 C7 C8 124.48(18) . . ?
N1 C7 C8 107.76(17) . . ?
N2 C8 C7 105.85(16) . . ?
N2 C8 H8 110.2 . . ?
N2 C8 C9 106.47(16) . . ?
C7 C8 H8 110.2 . . ?
C7 C8 C9 113.75(18) . . ?
C9 C8 H8 110.2 . . ?
C8 C9 H9A 111.2 . . ?
C8 C9 H9B 111.2 . . ?
H9A C9 H9B 109.1 . . ?
C10 C9 C8 102.74(18) . . ?
C10 C9 H9A 111.2 . . ?
C10 C9 H9B 111.2 . . ?
C9 C10 H10A 111.1 . . ?
C9 C10 H10B 111.1 . . ?
H10A C10 H10B 109.1 . . ?
C11 C10 C9 103.22(17) . . ?
C11 C10 H10A 111.1 . . ?
C11 C10 H10B 111.1 . . ?
N2 C11 C10 103.29(17) . . ?
N2 C11 H11A 111.1 . . ?
N2 C11 H11B 111.1 . . ?
C10 C11 H11A 111.1 . . ?
C10 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
N1 C12 H12 110.0 . . ?
N1 C12 C13 111.63(15) . . ?
N2 C12 N1 105.39(15) . . ?
N2 C12 H12 110.0 . . ?
N2 C12 C13 109.76(16) . . ?
C13 C12 H12 110.0 . . ?
N3 C13 C12 116.91(17) . . ?
N3 C13 C14 123.45(19) . . ?
C14 C13 C12 119.57(17) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 C13 118.45(19) . . ?
C15 C14 H14 120.8 . . ?
C14 C15 H15 120.5 . . ?
C16 C15 C14 119.0(2) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.82(19) . . ?
C17 C16 H16 120.6 . . ?
N3 C17 C16 122.50(19) . . ?
N3 C17 C18 115.86(18) . . ?
C16 C17 C18 121.63(18) . . ?
N4 C18 C17 116.41(19) . . ?
N4 C18 C19 122.6(2) . . ?
C19 C18 C17 120.97(19) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 C18 119.0(2) . . ?
C20 C19 H19 120.5 . . ?
C19 C20 H20 120.5 . . ?
C19 C20 C21 118.9(2) . . ?
C21 C20 H20 120.5 . . ?
C20 C21 H21 121.1 . . ?
C22 C21 C20 117.8(2) . . ?
C22 C21 H21 121.1 . . ?
N4 C22 C21 124.5(2) . . ?
N4 C22 H22 117.7 . . ?
C21 C22 H22 117.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C4 C5 C6 177.33(17) . . . . ?
O1 C7 C8 N2 179.88(18) . . . . ?
O1 C7 C8 C9 -63.6(3) . . . . ?
N1 C1 C2 C3 176.69(19) . . . . ?
N1 C1 C6 C5 -176.77(19) . . . . ?
N1 C7 C8 N2 -0.5(2) . . . . ?
N1 C7 C8 C9 116.07(19) . . . . ?
N1 C12 C13 N3 -19.7(2) . . . . ?
N1 C12 C13 C14 163.29(18) . . . . ?
N2 C8 C9 C10 -20.0(2) . . . . ?
N2 C12 C13 N3 96.7(2) . . . . ?
N2 C12 C13 C14 -80.2(2) . . . . ?
N3 C13 C14 C15 0.1(3) . . . . ?
N3 C17 C18 N4 178.45(19) . . . . ?
N3 C17 C18 C19 -1.6(3) . . . . ?
N4 C18 C19 C20 1.8(3) . . . . ?
C1 N1 C7 O1 -5.9(3) . . . . ?
C1 N1 C7 C8 174.47(17) . . . . ?
C1 N1 C12 N2 179.06(16) . . . . ?
C1 N1 C12 C13 -61.8(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C1 C6 C5 2.8(3) . . . . ?
C2 C3 C4 Cl1 -177.41(17) . . . . ?
C2 C3 C4 C5 2.2(3) . . . . ?
C3 C4 C5 C6 -2.3(3) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C6 C1 C2 C3 -2.9(3) . . . . ?
C7 N1 C1 C2 -179.59(19) . . . . ?
C7 N1 C1 C6 0.0(3) . . . . ?
C7 N1 C12 N2 -15.5(2) . . . . ?
C7 N1 C12 C13 103.57(18) . . . . ?
C7 C8 C9 C10 -136.16(18) . . . . ?
C8 N2 C11 C10 26.8(2) . . . . ?
C8 N2 C12 N1 14.61(19) . . . . ?
C8 N2 C12 C13 -105.73(17) . . . . ?
C8 C9 C10 C11 35.9(2) . . . . ?
C9 C10 C11 N2 -38.9(2) . . . . ?
C11 N2 C8 C7 117.22(18) . . . . ?
C11 N2 C8 C9 -4.1(2) . . . . ?
C11 N2 C12 N1 -107.37(19) . . . . ?
C11 N2 C12 C13 132.30(17) . . . . ?
C12 N1 C1 C2 -16.5(3) . . . . ?
C12 N1 C1 C6 163.07(19) . . . . ?
C12 N1 C7 O1 -170.4(2) . . . . ?
C12 N1 C7 C8 9.9(2) . . . . ?
C12 N2 C8 C7 -9.0(2) . . . . ?
C12 N2 C8 C9 -130.41(18) . . . . ?
C12 N2 C11 C10 148.15(18) . . . . ?
C12 C13 C14 C15 176.88(19) . . . . ?
C13 N3 C17 C16 1.9(3) . . . . ?
C13 N3 C17 C18 -177.39(17) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 N3 -1.0(3) . . . . ?
C15 C16 C17 C18 178.23(19) . . . . ?
C16 C17 C18 N4 -0.8(3) . . . . ?
C16 C17 C18 C19 179.2(2) . . . . ?
C17 N3 C13 C12 -178.29(17) . . . . ?
C17 N3 C13 C14 -1.4(3) . . . . ?
C17 C18 C19 C20 -178.18(19) . . . . ?
C18 N4 C22 C21 -1.1(4) . . . . ?
C18 C19 C20 C21 -1.5(3) . . . . ?
C19 C20 C21 C22 0.0(3) . . . . ?
C20 C21 C22 N4 1.4(4) . . . . ?
C22 N4 C18 C17 179.5(2) . . . . ?
C22 N4 C18 C19 -0.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.669
_oxdiff_exptl_absorpt_empirical_full_min 0.767
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cyl-b-43
_database_code_depnum_ccdc_archive 'CCDC 2292424'
loop_
_audit_author_name
_audit_author_address
ffg
;grfrf
China
;
_audit_update_record             
;
2023-09-02 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;
_audit_creation_date             2023-05-27
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H18 Br N O3'
_chemical_formula_sum            'C20 H18 Br N O3'
_chemical_formula_weight         400.26
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Br'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.49786(7)
_cell_length_b                   12.22987(9)
_cell_length_c                   14.93872(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1735.25(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7173
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      71.6020
_cell_measurement_theta_min      2.9660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.387
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8067
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.888
_diffrn_reflns_theta_min         4.673
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     88.00 119.00   0.50    0.50    --   42.10  77.00 -90.00   62
  2  ω     13.00 130.00   0.50    0.50    --   42.10  57.00 120.00  234
  3  ω     76.00 106.00   0.50    0.50    --   42.10  38.00 -90.00   60
  4  ω     -2.00  54.00   0.50    0.50    --   42.10  38.00 -90.00  112
  5  ω     88.00 131.00   0.50    0.50    --   42.10  77.00 -30.00   86
  6  ω     61.00 141.00   0.50    0.50    --  102.30 -82.00-120.00  160
  7  ω     22.00  49.00   0.50    0.50    --  102.30 -82.00-120.00   54
  8  ω     13.00 122.00   0.50    0.50    --  102.30 -64.00  60.00  218
  9  ω    125.00 182.00   0.50    0.50    --  102.30  82.00 150.00  114
 10  ω     13.00 133.00   0.50    0.50    --  102.30 -50.00  60.00  240
 11  ω     13.00 191.00   0.50    0.50    --  102.30  12.00  30.00  356
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0418050000
_diffrn_orient_matrix_UB_12      0.0823106000
_diffrn_orient_matrix_UB_13      -0.0734167000
_diffrn_orient_matrix_UB_21      0.0613442000
_diffrn_orient_matrix_UB_22      0.0939929000
_diffrn_orient_matrix_UB_23      0.0565345000
_diffrn_orient_matrix_UB_31      0.1442113000
_diffrn_orient_matrix_UB_32      -0.0161690000
_diffrn_orient_matrix_UB_33      -0.0452437000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                3293
_reflns_number_total             3324
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1370 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.015(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3324
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0209
_refine_ls_restrained_S_all      1.194
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0292P)²+0.7027P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0560
_refine_ls_wR_factor_ref         0.0561
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C17-O1 = C17-C16 = C17-C18
 1.45 with sigma of 0.01
 C18-C17
 1.35 with sigma of 0.01
 N1-H1
 0.87 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C19(H19A,H19B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15)
3.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.21545(3) 0.09967(2) 0.52570(2) 0.02835(9) Uani 1 1 d . . . . .
O1 O 0.1972(2) 0.19574(15) 0.09457(14) 0.0288(4) Uani 1 1 d D . . . .
O2 O 0.05956(19) 0.38785(17) 0.07432(14) 0.0272(4) Uani 1 1 d . . . . .
O3 O 0.2715(2) 0.47062(14) 0.06935(13) 0.0238(4) Uani 1 1 d . . . . .
N1 N 0.8665(2) 0.2058(2) 0.12098(17) 0.0242(5) Uani 1 1 d D . . . .
C1 C 0.7200(3) 0.06857(19) 0.15916(17) 0.0195(5) Uani 1 1 d . . . . .
C2 C 0.6875(3) -0.0393(2) 0.18443(18) 0.0217(5) Uani 1 1 d . . . . .
H2 H 0.592818 -0.060281 0.195719 0.026 Uiso 1 1 calc R U . . .
C3 C 0.7958(3) -0.1145(2) 0.19258(17) 0.0246(5) Uani 1 1 d . . . . .
H3 H 0.775115 -0.187230 0.210697 0.029 Uiso 1 1 calc R U . . .
C4 C 0.9356(3) -0.0850(2) 0.1745(2) 0.0271(6) Uani 1 1 d . . . . .
H4 H 1.007735 -0.138325 0.180201 0.033 Uiso 1 1 calc R U . . .
C5 C 0.9708(3) 0.0198(2) 0.14858(19) 0.0263(6) Uani 1 1 d . . . . .
H5 H 1.065425 0.039257 0.135339 0.032 Uiso 1 1 calc R U . . .
C6 C 0.8621(3) 0.0961(2) 0.14260(17) 0.0215(5) Uani 1 1 d . . . . .
C7 C 0.7312(3) 0.2463(2) 0.12331(19) 0.0229(5) Uani 1 1 d . . . . .
H7 H 0.706330 0.320130 0.111459 0.027 Uiso 1 1 calc R U . . .
C8 C 0.6378(3) 0.1658(2) 0.14499(17) 0.0212(5) Uani 1 1 d . . . . .
C9 C 0.4800(3) 0.1706(2) 0.15014(18) 0.0207(5) Uani 1 1 d . . . . .
H9 H 0.442521 0.112743 0.109315 0.025 Uiso 1 1 calc R U . . .
C10 C 0.4249(3) 0.1456(2) 0.24401(18) 0.0197(5) Uani 1 1 d . . . . .
C11 C 0.4794(3) 0.1982(2) 0.31927(18) 0.0220(5) Uani 1 1 d . . . . .
H11 H 0.557567 0.245927 0.312608 0.026 Uiso 1 1 calc R U . . .
C12 C 0.4219(3) 0.1823(2) 0.40368(18) 0.0232(5) Uani 1 1 d . . . . .
H12 H 0.460676 0.217958 0.454493 0.028 Uiso 1 1 calc R U . . .
C13 C 0.3066(3) 0.1134(2) 0.41252(18) 0.0223(5) Uani 1 1 d . . . . .
C14 C 0.2536(3) 0.0558(2) 0.3400(2) 0.0233(6) Uani 1 1 d . . . . .
H14 H 0.177286 0.006413 0.347347 0.028 Uiso 1 1 calc R U . . .
C15 C 0.3144(3) 0.0720(2) 0.25630(19) 0.0230(6) Uani 1 1 d . . . . .
H15 H 0.279953 0.031999 0.206401 0.028 Uiso 1 1 calc R U . . .
C16 C 0.4222(3) 0.2810(2) 0.11673(18) 0.0210(5) Uani 1 1 d D . . . .
H16A H 0.442244 0.337628 0.162308 0.025 Uiso 1 1 calc R U . . .
H16B H 0.472773 0.301628 0.061295 0.025 Uiso 1 1 calc R U . . .
C17 C 0.2676(3) 0.2801(2) 0.09804(17) 0.0230(5) Uani 1 1 d D . . . .
C18 C 0.1868(3) 0.3857(2) 0.07982(18) 0.0224(5) Uani 1 1 d D . . . .
C19 C 0.2027(3) 0.5746(2) 0.04626(18) 0.0249(6) Uani 1 1 d . . . . .
H19A H 0.126102 0.560696 0.002786 0.030 Uiso 1 1 calc R U . . .
H19B H 0.272063 0.623801 0.017535 0.030 Uiso 1 1 calc R U . . .
C20 C 0.1431(3) 0.6293(2) 0.1279(2) 0.0276(6) Uani 1 1 d . . . . .
H20A H 0.094232 0.696522 0.110206 0.041 Uiso 1 1 calc R U . . .
H20B H 0.219616 0.647308 0.169349 0.041 Uiso 1 1 calc R U . . .
H20C H 0.076465 0.579854 0.157383 0.041 Uiso 1 1 calc R U . . .
H1 H 0.939(2) 0.244(2) 0.107(2) 0.019(8) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C13 1.907(3) . ?
O1 C17 1.231(3) . ?
O2 C18 1.212(3) . ?
O3 C18 1.322(3) . ?
O3 C19 1.471(3) . ?
N1 C6 1.380(4) . ?
N1 C7 1.378(4) . ?
N1 H1 0.857(13) . ?
C1 C2 1.407(4) . ?
C1 C6 1.412(4) . ?
C1 C8 1.438(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.402(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.364(4) . ?
C8 C9 1.502(4) . ?
C9 H9 1.0000 . ?
C9 C10 1.528(4) . ?
C9 C16 1.540(4) . ?
C10 C11 1.395(4) . ?
C10 C15 1.394(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(4) . ?
C13 C14 1.386(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.392(4) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.495(4) . ?
C17 C18 1.527(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.502(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O3 C19 115.9(2) . . ?
C6 N1 H1 128(2) . . ?
C7 N1 C6 108.4(2) . . ?
C7 N1 H1 124(2) . . ?
C2 C1 C6 118.7(2) . . ?
C2 C1 C8 134.1(3) . . ?
C6 C1 C8 107.2(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 121.3 . . ?
C4 C5 C6 117.4(3) . . ?
C6 C5 H5 121.3 . . ?
N1 C6 C1 107.6(2) . . ?
N1 C6 C5 130.0(3) . . ?
C5 C6 C1 122.4(3) . . ?
N1 C7 H7 124.7 . . ?
C8 C7 N1 110.7(2) . . ?
C8 C7 H7 124.7 . . ?
C1 C8 C9 124.6(2) . . ?
C7 C8 C1 106.2(2) . . ?
C7 C8 C9 129.2(3) . . ?
C8 C9 H9 107.2 . . ?
C8 C9 C10 112.4(2) . . ?
C8 C9 C16 112.0(2) . . ?
C10 C9 H9 107.2 . . ?
C10 C9 C16 110.5(2) . . ?
C16 C9 H9 107.2 . . ?
C11 C10 C9 121.4(2) . . ?
C15 C10 C9 120.5(2) . . ?
C15 C10 C11 118.1(2) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.5(2) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.8(2) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 Br1 119.7(2) . . ?
C14 C13 Br1 118.9(2) . . ?
C14 C13 C12 121.4(2) . . ?
C13 C14 H14 120.7 . . ?
C13 C14 C15 118.6(2) . . ?
C15 C14 H14 120.7 . . ?
C10 C15 H15 119.3 . . ?
C14 C15 C10 121.5(2) . . ?
C14 C15 H15 119.3 . . ?
C9 C16 H16A 108.8 . . ?
C9 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C9 113.9(2) . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
O1 C17 C16 123.2(2) . . ?
O1 C17 C18 115.4(2) . . ?
C16 C17 C18 121.4(2) . . ?
O2 C18 O3 125.6(3) . . ?
O2 C18 C17 122.1(3) . . ?
O3 C18 C17 112.3(2) . . ?
O3 C19 H19A 109.4 . . ?
O3 C19 H19B 109.4 . . ?
O3 C19 C20 111.2(2) . . ?
H19A C19 H19B 108.0 . . ?
C20 C19 H19A 109.4 . . ?
C20 C19 H19B 109.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C13 C14 C15 175.58(19) . . . . ?
O1 C17 C18 O2 9.5(4) . . . . ?
O1 C17 C18 O3 -169.2(2) . . . . ?
N1 C7 C8 C1 1.3(3) . . . . ?
N1 C7 C8 C9 -176.1(3) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C1 C8 C9 C10 64.3(3) . . . . ?
C1 C8 C9 C16 -170.6(2) . . . . ?
C2 C1 C6 N1 -178.8(2) . . . . ?
C2 C1 C6 C5 1.4(4) . . . . ?
C2 C1 C8 C7 178.4(3) . . . . ?
C2 C1 C8 C9 -4.0(5) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C4 C5 C6 N1 178.2(3) . . . . ?
C4 C5 C6 C1 -2.1(4) . . . . ?
C6 N1 C7 C8 -0.6(3) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
C6 C1 C8 C7 -1.5(3) . . . . ?
C6 C1 C8 C9 176.1(2) . . . . ?
C7 N1 C6 C1 -0.3(3) . . . . ?
C7 N1 C6 C5 179.5(3) . . . . ?
C7 C8 C9 C10 -118.7(3) . . . . ?
C7 C8 C9 C16 6.4(4) . . . . ?
C8 C1 C2 C3 -179.6(3) . . . . ?
C8 C1 C6 N1 1.1(3) . . . . ?
C8 C1 C6 C5 -178.7(2) . . . . ?
C8 C9 C10 C11 49.9(3) . . . . ?
C8 C9 C10 C15 -132.5(3) . . . . ?
C8 C9 C16 C17 165.0(2) . . . . ?
C9 C10 C11 C12 174.7(2) . . . . ?
C9 C10 C15 C14 -173.7(2) . . . . ?
C9 C16 C17 O1 -11.9(4) . . . . ?
C9 C16 C17 C18 169.5(2) . . . . ?
C10 C9 C16 C17 -68.9(3) . . . . ?
C10 C11 C12 C13 -0.7(4) . . . . ?
C11 C10 C15 C14 3.9(4) . . . . ?
C11 C12 C13 Br1 -174.7(2) . . . . ?
C11 C12 C13 C14 3.7(4) . . . . ?
C12 C13 C14 C15 -2.8(4) . . . . ?
C13 C14 C15 C10 -1.1(4) . . . . ?
C15 C10 C11 C12 -3.0(4) . . . . ?
C16 C9 C10 C11 -76.0(3) . . . . ?
C16 C9 C10 C15 101.6(3) . . . . ?
C16 C17 C18 O2 -171.7(3) . . . . ?
C16 C17 C18 O3 9.6(4) . . . . ?
C18 O3 C19 C20 80.8(3) . . . . ?
C19 O3 C18 O2 -2.1(4) . . . . ?
C19 O3 C18 C17 176.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.107
_oxdiff_exptl_absorpt_empirical_full_min 0.905
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_bpy-1
_database_code_depnum_ccdc_archive 'CCDC 2295226'
loop_
_audit_author_name
_audit_author_address
ffg
;grfrf
China
;
_audit_update_record             
;
2023-09-15 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;
_audit_creation_date             2023-08-23
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 N4 O'
_chemical_formula_sum            'C22 H20 N4 O'
_chemical_formula_weight         356.42
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.83171(10)
_cell_length_b                   16.1053(2)
_cell_length_c                   16.2446(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1787.34(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14857
_cell_measurement_temperature    126(10)
_cell_measurement_theta_max      77.0000
_cell_measurement_theta_min      2.6570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15544
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.061
_diffrn_reflns_theta_min         3.865
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      126(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00  68.00   0.50    0.50    --  105.91 -57.00-150.00   64
  2  ω     34.00  59.00   0.50    0.50    --  105.91 -57.00 -60.00   50
  3  ω     34.00  59.00   0.50    0.50    --  105.91 -58.00  68.00   50
  4  ω     98.00 163.00   0.50    0.50    --  105.91  38.00  30.00  130
  5  ω     98.00 162.00   0.50    0.50    --  105.91  74.00  65.00  128
  6  ω    -25.00  10.00   0.50    0.30    --   48.03 -19.00 -60.00   70
  7  ω     49.00  75.00   0.50    0.50    --  105.91 -93.00-161.00   52
  8  ω     38.00 106.00   0.50    0.50    --  105.91 -99.00 -60.00  136
  9  ω     39.00  98.00   0.50    0.50    --  105.91 -99.00 150.00  118
 10  ω    -67.00  22.00   0.50    0.30    --  -48.03  74.00  65.00  178
 11  ω    -22.00   3.00   0.50    0.30    --  -48.03  19.00 -30.00   50
 12  ω    -10.00  26.00   0.50    0.30    --  -48.03  19.00-150.00   72
 13  ω     -4.00  26.00   0.50    0.30    --  -48.03  19.00-180.00   60
 14  ω    -64.00 -33.00   0.50    0.50    -- -104.00  58.00-150.00   62
 15  ω    -64.00 -33.00   0.50    0.50    -- -104.00  57.00  30.00   62
 16  ω    -61.00 -35.00   0.50    0.50    -- -104.00  57.00  60.00   52
 17  ω    -63.00 -37.00   0.50    0.50    -- -104.00  57.00 120.00   52
 18  ω   -170.00-106.00   0.50    0.50    -- -104.00 -38.00   0.00  128
 19  ω   -147.00-121.00   0.50    0.50    -- -104.00 -58.00  68.00   52
 20  ω    -98.00 -73.00   0.50    0.30    --  -48.03 -74.00 -62.00   50
 21  ω     34.00 120.00   0.50    0.30    --   48.03  58.00-150.00  172
 22  ω     34.00 120.00   0.50    0.30    --   48.03  57.00 -60.00  172
 23  ω     38.00 120.00   0.50    0.30    --   48.03  38.00-180.00  164
 24  ω     34.00 120.00   0.50    0.30    --   48.03  57.00   0.00  172
 25  ω     28.00 120.00   0.50    0.30    --   48.03  74.00  65.00  184
 26  ω   -175.00-104.00   0.50    0.50    -- -104.00 -19.00-120.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1832764000
_diffrn_orient_matrix_UB_12      -0.0503421000
_diffrn_orient_matrix_UB_13      0.0236205000
_diffrn_orient_matrix_UB_21      0.0049410000
_diffrn_orient_matrix_UB_22      0.0435200000
_diffrn_orient_matrix_UB_23      0.0844085000
_diffrn_orient_matrix_UB_31      -0.1313193000
_diffrn_orient_matrix_UB_32      -0.0686975000
_diffrn_orient_matrix_UB_33      0.0362196000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.934
_reflns_number_gt                3592
_reflns_number_total             3620
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1468 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(11)
_refine_ls_extinction_coef       0.0072(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3620
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0335P)²+0.4245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0712
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16),
 C19(H19), C20(H20), C21(H21), C22(H22)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3258(2) 0.16611(9) 0.82369(8) 0.0389(3) Uani 1 1 d . . . . .
N1 N 0.6296(2) 0.19450(8) 0.76598(8) 0.0190(3) Uani 1 1 d . . . . .
N2 N 0.60363(19) 0.11632(8) 0.64561(8) 0.0201(3) Uani 1 1 d . . . . .
N3 N 0.55334(19) 0.30858(8) 0.64060(8) 0.0185(3) Uani 1 1 d . . . . .
N4 N 0.3528(2) 0.50005(9) 0.56247(9) 0.0274(3) Uani 1 1 d . . . . .
C1 C 0.7167(2) 0.24708(9) 0.82576(9) 0.0202(3) Uani 1 1 d . . . . .
C2 C 0.8988(3) 0.28243(11) 0.81013(10) 0.0296(4) Uani 1 1 d . . . . .
H2 H 0.963659 0.271280 0.759595 0.036 Uiso 1 1 calc R U . . .
C3 C 0.9861(3) 0.33387(12) 0.86798(12) 0.0349(4) Uani 1 1 d . . . . .
H3 H 1.109797 0.358161 0.856441 0.042 Uiso 1 1 calc R U . . .
C4 C 0.8950(3) 0.35014(11) 0.94223(11) 0.0337(4) Uani 1 1 d . . . . .
H4 H 0.954044 0.386122 0.981340 0.040 Uiso 1 1 calc R U . . .
C5 C 0.7171(3) 0.31334(11) 0.95861(11) 0.0318(4) Uani 1 1 d . . . . .
H5 H 0.655693 0.322980 1.010211 0.038 Uiso 1 1 calc R U . . .
C6 C 0.6256(3) 0.26248(10) 0.90130(10) 0.0252(4) Uani 1 1 d . . . . .
H6 H 0.502052 0.238311 0.913337 0.030 Uiso 1 1 calc R U . . .
C7 C 0.4448(3) 0.16149(10) 0.76838(10) 0.0238(3) Uani 1 1 d . . . . .
C8 C 0.4133(2) 0.11545(10) 0.68775(10) 0.0235(3) Uani 1 1 d . . . . .
H8 H 0.312555 0.144546 0.653649 0.028 Uiso 1 1 calc R U . . .
C9 C 0.3580(3) 0.02337(11) 0.69866(12) 0.0352(4) Uani 1 1 d . . . . .
H9A H 0.364149 0.006975 0.757338 0.042 Uiso 1 1 calc R U . . .
H9B H 0.224549 0.012432 0.677562 0.042 Uiso 1 1 calc R U . . .
C10 C 0.5105(3) -0.02310(11) 0.64835(13) 0.0361(4) Uani 1 1 d . . . . .
H10A H 0.537054 -0.078623 0.671994 0.043 Uiso 1 1 calc R U . . .
H10B H 0.468015 -0.029551 0.590435 0.043 Uiso 1 1 calc R U . . .
C11 C 0.6886(3) 0.03263(10) 0.65464(12) 0.0300(4) Uani 1 1 d . . . . .
H11A H 0.754420 0.026203 0.708564 0.036 Uiso 1 1 calc R U . . .
H11B H 0.783591 0.020730 0.610149 0.036 Uiso 1 1 calc R U . . .
C12 C 0.7178(2) 0.18214(9) 0.68417(9) 0.0181(3) Uani 1 1 d . . . . .
H12 H 0.856872 0.163781 0.690427 0.022 Uiso 1 1 calc R U . . .
C13 C 0.7093(2) 0.25992(9) 0.63076(9) 0.0182(3) Uani 1 1 d . . . . .
C14 C 0.8540(2) 0.27418(10) 0.57230(9) 0.0221(3) Uani 1 1 d . . . . .
H14 H 0.962043 0.237450 0.566839 0.027 Uiso 1 1 calc R U . . .
C15 C 0.8365(3) 0.34346(11) 0.52217(10) 0.0248(4) Uani 1 1 d . . . . .
H15 H 0.933396 0.355405 0.481936 0.030 Uiso 1 1 calc R U . . .
C16 C 0.6758(2) 0.39500(10) 0.53155(10) 0.0228(3) Uani 1 1 d . . . . .
H16 H 0.660569 0.442781 0.497858 0.027 Uiso 1 1 calc R U . . .
C17 C 0.5367(2) 0.37546(10) 0.59141(9) 0.0192(3) Uani 1 1 d . . . . .
C18 C 0.3601(2) 0.42811(9) 0.60454(9) 0.0202(3) Uani 1 1 d . . . . .
C19 C 0.2116(2) 0.40302(10) 0.65751(10) 0.0229(3) Uani 1 1 d . . . . .
H19 H 0.221220 0.351968 0.686521 0.027 Uiso 1 1 calc R U . . .
C20 C 0.0497(3) 0.45368(11) 0.66727(10) 0.0269(4) Uani 1 1 d . . . . .
H20 H -0.054764 0.437267 0.702292 0.032 Uiso 1 1 calc R U . . .
C21 C 0.0414(3) 0.52856(11) 0.62545(11) 0.0279(4) Uani 1 1 d . . . . .
H21 H -0.066882 0.565033 0.631773 0.034 Uiso 1 1 calc R U . . .
C22 C 0.1959(3) 0.54837(11) 0.57425(12) 0.0307(4) Uani 1 1 d . . . . .
H22 H 0.190406 0.599690 0.545505 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.214(2) . ?
N1 C1 1.419(2) . ?
N1 C7 1.370(2) . ?
N1 C12 1.4728(19) . ?
N2 C8 1.470(2) . ?
N2 C11 1.475(2) . ?
N2 C12 1.4576(19) . ?
N3 C13 1.332(2) . ?
N3 C17 1.346(2) . ?
N4 C18 1.346(2) . ?
N4 C22 1.338(2) . ?
C1 C2 1.392(2) . ?
C1 C6 1.398(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.521(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.540(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.521(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.516(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12 1.0000 . ?
C12 C13 1.525(2) . ?
C13 C14 1.390(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.396(2) . ?
C17 C18 1.490(2) . ?
C18 C19 1.390(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.381(3) . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C12 121.76(13) . . ?
C7 N1 C1 126.74(14) . . ?
C7 N1 C12 110.51(12) . . ?
C8 N2 C11 107.05(13) . . ?
C12 N2 C8 106.28(12) . . ?
C12 N2 C11 114.27(13) . . ?
C13 N3 C17 117.85(13) . . ?
C22 N4 C18 117.22(15) . . ?
C2 C1 N1 119.61(14) . . ?
C2 C1 C6 119.04(15) . . ?
C6 C1 N1 121.33(15) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.33(17) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.70(18) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 118.96(17) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.40(17) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.54(17) . . ?
C5 C6 H6 120.2 . . ?
O1 C7 N1 127.90(15) . . ?
O1 C7 C8 124.92(15) . . ?
N1 C7 C8 107.18(13) . . ?
N2 C8 C7 105.73(13) . . ?
N2 C8 H8 110.3 . . ?
N2 C8 C9 106.24(14) . . ?
C7 C8 H8 110.3 . . ?
C7 C8 C9 113.90(14) . . ?
C9 C8 H8 110.3 . . ?
C8 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
C10 C9 C8 104.13(15) . . ?
C10 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
C9 C10 H10A 111.2 . . ?
C9 C10 H10B 111.2 . . ?
H10A C10 H10B 109.1 . . ?
C11 C10 C9 102.84(14) . . ?
C11 C10 H10A 111.2 . . ?
C11 C10 H10B 111.2 . . ?
N2 C11 C10 102.61(15) . . ?
N2 C11 H11A 111.2 . . ?
N2 C11 H11B 111.2 . . ?
C10 C11 H11A 111.2 . . ?
C10 C11 H11B 111.2 . . ?
H11A C11 H11B 109.2 . . ?
N1 C12 H12 109.7 . . ?
N1 C12 C13 112.74(12) . . ?
N2 C12 N1 105.48(12) . . ?
N2 C12 H12 109.7 . . ?
N2 C12 C13 109.41(12) . . ?
C13 C12 H12 109.7 . . ?
N3 C13 C12 116.46(13) . . ?
N3 C13 C14 123.62(14) . . ?
C14 C13 C12 119.81(14) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 C13 118.21(15) . . ?
C15 C14 H14 120.9 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.10(15) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.77(14) . . ?
C17 C16 H16 120.6 . . ?
N3 C17 C16 122.44(14) . . ?
N3 C17 C18 116.04(13) . . ?
C16 C17 C18 121.52(14) . . ?
N4 C18 C17 116.57(14) . . ?
N4 C18 C19 122.51(15) . . ?
C19 C18 C17 120.92(14) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 C18 118.88(15) . . ?
C20 C19 H19 120.6 . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.32(16) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 121.1 . . ?
C22 C21 C20 117.72(16) . . ?
C22 C21 H21 121.1 . . ?
N4 C22 C21 124.33(16) . . ?
N4 C22 H22 117.8 . . ?
C21 C22 H22 117.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C8 N2 -172.00(16) . . . . ?
O1 C7 C8 C9 -55.7(2) . . . . ?
N1 C1 C2 C3 -179.89(17) . . . . ?
N1 C1 C6 C5 179.06(15) . . . . ?
N1 C7 C8 N2 7.30(17) . . . . ?
N1 C7 C8 C9 123.56(16) . . . . ?
N1 C12 C13 N3 -33.62(19) . . . . ?
N1 C12 C13 C14 150.01(14) . . . . ?
N2 C8 C9 C10 -8.90(18) . . . . ?
N2 C12 C13 N3 83.42(16) . . . . ?
N2 C12 C13 C14 -92.95(17) . . . . ?
N3 C13 C14 C15 0.9(2) . . . . ?
N3 C17 C18 N4 172.64(14) . . . . ?
N3 C17 C18 C19 -7.6(2) . . . . ?
N4 C18 C19 C20 0.2(2) . . . . ?
C1 N1 C7 O1 -5.2(3) . . . . ?
C1 N1 C7 C8 175.49(14) . . . . ?
C1 N1 C12 N2 172.23(13) . . . . ?
C1 N1 C12 C13 -68.43(18) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -1.9(3) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C6 C1 C2 C3 -1.6(2) . . . . ?
C7 N1 C1 C2 -173.35(15) . . . . ?
C7 N1 C1 C6 8.4(2) . . . . ?
C7 N1 C12 N2 -18.38(16) . . . . ?
C7 N1 C12 C13 100.96(15) . . . . ?
C7 C8 C9 C10 -124.87(16) . . . . ?
C8 N2 C11 C10 36.62(17) . . . . ?
C8 N2 C12 N1 22.27(15) . . . . ?
C8 N2 C12 C13 -99.26(14) . . . . ?
C8 C9 C10 C11 30.66(19) . . . . ?
C9 C10 C11 N2 -41.33(18) . . . . ?
C11 N2 C8 C7 104.13(15) . . . . ?
C11 N2 C8 C9 -17.23(17) . . . . ?
C11 N2 C12 N1 -95.57(15) . . . . ?
C11 N2 C12 C13 142.90(14) . . . . ?
C12 N1 C1 C2 -5.8(2) . . . . ?
C12 N1 C1 C6 175.97(14) . . . . ?
C12 N1 C7 O1 -173.97(17) . . . . ?
C12 N1 C7 C8 6.76(17) . . . . ?
C12 N2 C8 C7 -18.39(16) . . . . ?
C12 N2 C8 C9 -139.75(13) . . . . ?
C12 N2 C11 C10 154.01(14) . . . . ?
C12 C13 C14 C15 176.97(14) . . . . ?
C13 N3 C17 C16 -0.1(2) . . . . ?
C13 N3 C17 C18 179.99(13) . . . . ?
C13 C14 C15 C16 -0.6(2) . . . . ?
C14 C15 C16 C17 0.1(2) . . . . ?
C15 C16 C17 N3 0.3(2) . . . . ?
C15 C16 C17 C18 -179.81(14) . . . . ?
C16 C17 C18 N4 -7.3(2) . . . . ?
C16 C17 C18 C19 172.49(15) . . . . ?
C17 N3 C13 C12 -176.71(13) . . . . ?
C17 N3 C13 C14 -0.5(2) . . . . ?
C17 C18 C19 C20 -179.50(15) . . . . ?
C18 N4 C22 C21 -1.0(3) . . . . ?
C18 C19 C20 C21 -1.3(2) . . . . ?
C19 C20 C21 C22 1.2(3) . . . . ?
C20 C21 C22 N4 0.0(3) . . . . ?
C22 N4 C18 C17 -179.38(15) . . . . ?
C22 N4 C18 C19 0.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.699
_oxdiff_exptl_absorpt_empirical_full_min 0.490
